Hydrazine → HCID 22466720, compound

HRID 612270Notes

Reaction equation

HRID 612270 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:23]#[N:24])=[CH:5][CH:4]=1.NN>[Pd]>[NH2:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][C:11]([C:23]#[N:24])=[C:10]2[NH:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:25])[CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22466751HCID 22466751, compound

Product 1

HCID 22466720HCID 22466720, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Prepared from 4-(4-dimethylaminophenylamino)-6-nitroquinoline-3-carbonitrile (5.00 g), 1.20 g of anhyd hydrazine and 0.500 g of 10% Pd/C in the same manner as Example 388 155179. After washing first with MeOH (discarded), the product was eluted with DMF. The latter solvent was collected separately, evaporated and the residue was dried in vacuo (50° C.). The yield of 6-amino-4-(4-dimethylaminophenylamino)quinoline-3-carbonitrile was 4.00 g as a yellow solid: mass spectrum (electrospray, m/e): M+H 303.9.

Workup

  1. washAfter washing first with MeOH (discarded)
  2. washthe product was eluted with DMF
  3. customThe latter solvent was collected separately
  4. customevaporated
  5. customthe residue was dried in vacuo (50° C.)

Sources & evidence

ORD record
ord-b223ef843df1475da37888a631c9b979
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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